If you haven't read parts 1-3, you need to. There's nothing more boring for a reader than a recap and I won't be repeating Molly's and my ritual.
Molly and I had an arrangement that if I wasn't dressed in a robe or she brought our cups of tea still dressed in her leggings and sensible top, it meant we reverted to tea, chat and card or board games.
At our disparate ages and genders we had different reasons to 'not be on' and we'd agreed no questions would be asked. That had been the situation for the past week.
This day though, Molly had brought her own uniform. It consisted of a mid thigh length leather skirt. Nothing else. Her perky breasts were on full display and her long stiff nipples told a story of their own. She brought our tea and unconventionally served mine from her side of the coffee table.
As she set mine down she said, "Take your robe off please Mr Wilson." Her expression was a mixture of her usual youthful exuberance and confidence, expectant excitement and a little apprehension.
I raised an eyebrow at her 'impertinence' and her face broke out into a more relaxed cheeky smile. "I like to see you naked, Mr Wilson."
I did as requested. She remarked, "I haven't seen you like this before," referring to my flaccid state, "I'm glad you're like that today. I'll get to see you grow."
This was all far removed from our usual games. She sipped her tea and said, "I've got a few personal issues to talk to you about Mr Wilson. I know I can trust your discretion to protect my privacy and not discuss what I'm about to tell you with anybody else." I was wondering where this was going. We'd always had fun and this sounded serious. I nodded in agreement and smiled in a comforting way to encourage her.
"The first thing you should know is that, technically, I'm a virgin. I've had my cherry popped. I've had dildoes, vibrators and even fruit inside my pussy, but never a real live flesh and blood cock."
I nodded and hoped my facial expressions encouraged her to feel safe and open up. I've got a real soft spot for Molly, as well as a growing hard spot as my cock head emerged from its protective foreskin at the thought of what might be coming.
Molly dampened my cock's enthusiasm a little as she continued, "And I'd like to keep it that way for now. The thing is, I have a really strong need to be penetrated by a real live cock." I was a bit confused.
"You see, I've been watching a fair bit of anal porn lately," she now had my cock's full attention back as it started to grow and stiffen again. Molly watched it and giggled. I think that made her feel more relaxed than any nodding or facial expressions.
She continued, "It turns me on..... a lot. But most of what I've seen is really rough and abusive and that's not what I want."
I've learned enough about women in my 61 years to know that know was not the time to say anything but, "Go on."
"I want my first time to be with somebody who'll be gentle. Somebody with enough experience to introduce me to it in a way that I'll enjoy it."
Her slight pause was my invitation to contribute. "I think you're being really sensible in both respects, Molly. Most people's experience in losing their virginity isn't usually fantastic. They usually ponder on it for a long time, build great expectations and imagine a wonderful experience and when it happens it's often clumsy and forgettable."
"A first anal experience, just because of the nature of it, can be even worse or better depending on how it's handled."
She smiled widely, "I knew you'd understand Mr Wilson."
As I continued Molly's right hand toyed with her right nipple and her knees parted, affording me a lovely view up her skirt, showing me her pantiless pussy.
"I can tell you from experience that an anal deflowering can be an awful experience, but done the right way, can be a wonderful experience."
Molly was very enthusiastic, "Let's get started then!"
I was more hesitant, "Hang on a minute sweetie. There are some........ aids that I don't have on hand and we shouldn't rush it without them."
Molly giggled again and grabbed her bag. She emptied it onto the lounge beside her. "I've thought about that. Will these do?"
She had some vital equipment like lubricant and oil, some that could be helpful like some vibrators of varying sizes and some that weren't necessary like condoms and an anal bead wand that might be fun at a later time.
I said, "You're well prepared Molly. So, you're 100% certain about this then?"
She nodded and replied, "I'm absolutely sure. I'm really excited about it and very nervous at the same time, but you're the only person in the world I trust to do it Mr Wilson. I know you'll be gentle and try not to hurt me."
I felt a sense of pride in Molly's trust in me and responsibility to make sure I made her first anal experience one that would be memorable for her and make her want more. The last part of that had some selfish motivation, I have to say.
"Then let's go to the guest room and make use of the bed Molly. That will be more comfortable than our usual playground out here," I said as I stood up and held out my hand to take hers.
She quickly gathered her accoutrements and took my hand, which I squeezed to give her comfort in the knowledge she was safe in mine.
